Caitlin Long (Avanti Financial Group) on Bitcoin banks and the Wyoming SPDI (EP. 101)
On The Brink with Castle Island
Release Date: 07/13/2020
Weekly Roundup 12/19/25 (Quantum FUD, CLARITY markup, are forks obsolete?) (EP.692)
On The Brink with Castle Island
Matt and Nic are back for more deals and news. In this episode: Secret exchange insolvency rumors Caroline Ellison is free David Sacks says CLARITY is getting a markup The Fed rescinds their 2023 Novel Activities Supervision program Insolvent exchange prediction markets Visa’s stablecoin advisory business JPM launches a tokenized Treasury fund MONY Quantum FUD Why Quantum might be a surprise Bitwise 2026 predictions The four year cycle is over Grabby aliens and the Dark Forest Content mentioned in this episode: Talos and Factset,
info_outline
Corn (Yearn Finance) on the Evolution of DeFi Protocols (EP. 691)
On The Brink with Castle Island
Henry sits down with , head of business development at , for a conversation about the evolution and current state of defi. In this episode: The history of defi from 2020 to today, and how the TerraLuna crash impacted the market How incentive mechanisms in defi have changed in 2025 What caused the collapse of xUSD and Stream Finance? What is the role of risk curators in defi? The state of onchain cybersecurity and recent hacks What is the appetite for defi from non-crypto users and institutions, and will a declining fed funds rate help? How do defi protocols drive value to their native...
info_outline
Weekly Roundup 12/12/25 (Do Kwon sentenced, DTC no action letter, Circle’s private stablecoin) (EP.690)
On The Brink with Castle Island
Matt and Nic are back with more news and deals. In this episode: CIV grows the team Nic does not regret 8 years in crypto People are getting blackpilled about crypto Does speculation in crypto have positive externalities? Matt has never seen LOTR Will web3 ever come back? The OCC lets banks broker crypto trades The Bitwise 10 lists Rushi Manche returns with a fund Circle is launching a private stablecoin The DTC gets a no action letter from the SEC to settle tokenized securities We do a Terra/Luna restrospective Terra’s fatal mistake Oracle mishaps on prediction markets Why did the...
info_outline
Weekly Roundup 12/05/25 (The trouble with Taproot, a prediction market paradox, HFSC OCP.2 report) (EP.689)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Quantum risk again Are banks filled with spooks? The trouble with Taproot addresses Microstrategy’s dollar reserve Kalshi is going on chain Prediction market predicaments Are insiders monetizing Google search information on Polymarket? Are prediction markets insider trading machines by definition? DAT activist fights Vanguard adds Bitcoin ETFs House Financial Services Committee releases their final report on OCP2.0 What’s going on with leverage in crypto? Are AI agents going to start stealing crypto? Is...
info_outline
Stepan Simkin (Squads) on Stablecoin-Powered Financial Services (EP.688)
On The Brink with Castle Island
, founder of , sits down with Wyatt on today's episode. In this discussion: Squads' evolution from a DeFi-facing product to servicing a broader range of companies' asset treasury needs. What are the pain points of local small-medium businesses? What is driving the gradual global movement from local currencies into USD stablecoins? The appetite for safe yield across user types. Other traditional digital banking players and how they are evolving with technology. How the stablecoin trend impacts governments. What happens to local banks?
info_outline
Weekly Roundup 11/27/25 (Who we are thankful for, S&P downgrades Tether) (EP.687)
On The Brink with Castle Island
Matt and Nic record a special Thanksgiving episode of OTB. In this episode: What’s the deal with deep fried turkeys? Polymarket gets CTFC approval Klarna is launching a stablecoin on Tempo Upbit is hacked Berachain drama Tether gets a downgrade from S&P Robinhood is spinning up their own prediction market with Susquehanna Are Visa and Mastercard moving fast enough? Who are we thankful for?
info_outline
Weekly Roundup 11/21/25 (Quantum FUD, DAT hangover, stablecoin duration risk) (EP.686)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: Is Quantum FUD causing Bitcoin to sell off? Ray Dalio is worry about Quantum Scott Aaronson is worried about quantum computing Vitalik is worried about quantum Quantum upgrade scenarios Are we still suffering from the flash crash? The DATs are selling DAT spot arbitrage Will the US government end up with the Satoshi coins Should the government bail out AI? Will NFTs come back? IBIT is Harvard’s largest 13F position David Frum on stablecoins Will stablecoins require a bailout?
info_outline
Weekly Roundup 11/14/25 (Miran speech, Cash App adds Stables, DAT Hangover)(EP.685)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: The Senate Ag Cmte publishes a Market Structure draft Paul Atkins’ token taxonomy speech Fed Governor Stephen Miran gives a major stablecoin speech Grayscale files their S-1 Coinbase announces a tokensale platform Coinbase is leaving Delaware The Coinbase BVNK deal falls through Visa Direct adds stablecoin support The Czech republic buys Bitcoin DATs are struggling CBDC holdouts Jack Dorsey bends the knee on stablecoins Content mentioned: Stephen Miran,
info_outline
Weekly Roundup 11/07/25 (Balancer hack, DATs are suffering, Zcash rally) (EP.684)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Tom Brady’s clone dog We reminisce on the Nic Carter v Mike Green debate Is the government shutdown draining market liquidity? The trouble with Opendimes Balancer hacked Stream finance’s xUSD collapses DATs are selling coins Why is Zcash rallying? Are stablecoins the lightbulb of crypto Content mentioned: JW Verret,
info_outline
Keone Hon (Monad Foundation) on Blockchains Built to Scale (EP.683)
On The Brink with Castle Island
, founder of the Foundation joins the show. In this episode: From the point of view of Keone's trading background, what is the promise of blockchains? Reimagining financial systems with blockchains in 2025 Why build Monad, and for anyone using a chain, why use Monad? How the importance of decentralization and chain efficiency becomes underscored during fragile market periods Auto-Deleveraging (ADL): What it is and why it is important. Where is there economic efficiency to be created? How has Keone gone about building a team to tackle this challenge? What would make Monad "successful" in 2-3...
info_outlineCaitlin Long, founder and CEO of Avanti Financial Group, joins the show. Caitlin is a thinker and writer we admire a huge amount and she has done a monumental job with her advocacy for responsible custody practices among crypto depository institutions. She is one of the key architects of the Wyoming Special Purpose Depository Institution legislation which establishes a new form of crypto bank in Wyoming. In in no small part thanks to her efforts that Wyoming is the most progressive state in terms of defining and regulating digital assets and the institutions that custody them. We share Caitlin's enthusiasm for clarifying depositor exchange relationships and for public-facing proofs of reserve, so we were very excited have her on the show. Covered in this episode:
- Risks involved in complying with the FATF's travel rule
- How the FATF enforces its recommendations
- Why compliance burdens freeze out small and community banks
- How the $10k limit for disclosure for cash transactions increases the scope of transactions that should be disclosed in real terms
- How the Bank Secrecy Act and the third party doctrine means the government can procure warrantless financial data
- Caitlin's Bitcoin origin story
- The thawing of the gold community's sentiments towards bitcoin
- The tension inherent in the institutionalization of bitcoin
- Why Proofs of Reserves aren't more popular today
- The importance of distinguishing ownership of a key and a legal title
- Why users are poorly equipped to hold exchanges accountable
- Why the state by state regulation in the US doesn't suit the reality of crypto custodians
- How the Wyoming SPDI legislation got started
- What the Wyoming SPDI laws actually mean
- How Avanti got its name
- Caitlin's long term objectives with Avanti
- Why banking remains the achilles heel of the crypto industry
- Why existing banks might not be able to handle future growth of the crypto industry
- How the FDIC targeted the crypto industry
- Why custodians should have access to the Fed window
- Caitlin's pitch to entrepreneurs to move to Wyoming